Succinic anhydride → HCID 86641464, compound

HRID 2427165Notes

Reaction equation

[CH3:1][N:2]1[C@:6]([CH2:13][OH:14])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5](=[O:15])[N:4]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=2)[C:3]1=[O:28].CN(C1C=CC=CN=1)C.[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH2:40][CH2:39]1>N1C=CC=CC=1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:4]2[C:5](=[O:15])[C:6]([CH2:13][O:14][C@@H:40]([CH2:39][CH:38]=[O:44])[C:41]([OH:43])=[O:42])([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:2]([CH3:1])[C:3]2=[O:28])=[CH:17][C:18]=1[C:24]([F:25])([F:27])[F:26])#[N:21]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 0.60 g of (S)-4-[3-methyl-4-hydroxymethyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile in 24 mL of pyridine was added 19 mg of dimethylaminopyridine and 1.54 g of succinic anhydride. The mixture is stirred at 110° C. for 7 hours then evaporated to dryness. The crude product is washed with water and extracted with dichloromethane. The organic layer is dried over magnesium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 50/50 heptane/ethyl acetate to give the desired compound.

Workup

customthen evaporated to dryness
washThe crude product is washed with water
extractionextracted with dichloromethane
dry with materialThe organic layer is dried over magnesium sulfate
filtrationfiltered
customevaporated
customThe crude product is purified by chromatography over silica gel
washwhile eluting with 50/50 heptane/ethyl acetate

Sources & evidence

ORD record: ord-efef43112bde497ebd6160579effc010
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968581B2

Reaction notes

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